Company Overview
Connesso Inc. is a modern Managed Service Provider (MSP) based in Ontario, delivering secure, scalable IT solutions for small to mid-sized businesses. We specialize in Microsoft 365, cloud infrastructure, network design, cybersecurity, and fully managed IT support.
We’re growing—and looking for a results-driven sales professional to help expand our client base and drive long-term managed services relationships.
Role Summary
We are seeking a highly motivated B2B Sales Executive to identify, prospect, and onboard new clients for our Managed IT Services. This is a hunter role focused on generating new business opportunities, building relationships, and closing recurring monthly service agreements (MRR)
Key Responsibilities
- Identify and prospect new SMB clients (20–100 users ideally)
- Generate leads through:
- Cold outreach (phone, email, LinkedIn)
- Networking and local business engagement
- Referrals and partnerships
- Conduct discovery calls to understand client IT needs, risks, and business goals
- Present and position Connesso’s Managed Services offerings
- Develop and deliver proposals/MSAs and follow up to close deals
- Maintain pipeline and activity in CRM (Autotask or equivalent)
- Collaborate with the technical team for scoping and onboarding handoff
- Meet or exceed monthly and quarterly sales targets
What Success Looks Like (KPIs)
- New Monthly Recurring Revenue (MRR) generated
- Number of qualified pipeline opportunities
- Close rate and sales cycle speed
- Client retention post-onboarding
- Consistent outbound activity (calls, meetings, demos)
Qualifications
Required
- 5+ years of B2B sales experience (preferably in IT/MSP/SaaS)
- Proven track record of closing new business
- Strong communication, negotiation, and presentation skills
- Comfortable with outbound prospecting and cold outreach
Preferred
- Experience selling:
- Managed IT Services / MSP offerings
- Microsoft 365 / cloud solutions
- Cybersecurity or networking services
- Familiarity with SMB IT environments
- Experience using Autotask CRM/PSA tools
Compensation
- Base Salary: $50,000 – $70,000 (depending on experience)
- Commission: Uncapped (based on MRR closed)
- OTE: $80,000 – $120,000+
- Performance bonuses tied to revenue milestones
Benefits
- Flexible work environment (hybrid/remote options)
- Career growth into senior sales or leadership roles
- Work with a fast-growing, modern MSP
- Support from the technical and operations team
Pay: From $50,000.00 per year
Benefits:
- Dental care
- Extended health care
- Vision care
Application question(s):
- What is the largest deal (MRR or contract value) you’ve closed?
- Are you comfortable with cold outreach and prospecting?
Experience:
- selling managed IT services or MSP offerings: 5 years (preferred)
- B2B sales: 5 years (preferred)
Licence/Certification:
- Driving Licence (preferred)
Work Location: Hybrid remote in Mississauga, ON L5T 1X3
